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Deck 17: Benzene and Aromatic Compounds
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Question
Which of the following molecules has the most acidic hydrogen atoms? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
Which of the following ions is aromatic? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
How many 13CNMR signals does the following compound exhibit? 
A) 4
B) 5
C) 6
D) 8
A) 4
B) 5
C) 6
D) 8
Question
Question
What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives? 
A) I = 3 signals; II = 3 signals; III = 2 signals.
B) I = 3 signals; II = 4 signals; III = 2 signals.
C) I = 6 signals; II = 6 signals; III = 6 signals.
D) I = 3 signals; II = 4 signals; III = 3 signals.
A) I = 3 signals; II = 3 signals; III = 2 signals.
B) I = 3 signals; II = 4 signals; III = 2 signals.
C) I = 6 signals; II = 6 signals; III = 6 signals.
D) I = 3 signals; II = 4 signals; III = 3 signals.
Question
Rank the following compounds in order of decreasing acidity, starting with the most acidic. 
A) I > II > III
B) III > II > I
C) III > I > II
D) I > III > II
A) I > II > III
B) III > II > I
C) III > I > II
D) I > III > II
Question
What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150 2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm. 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
Question
What is the IUPAC name of the following compound? 
A) 3,6-Dichloroaniline
B) 2,5-Dichloroaniline
C) 2,5-Dichloroaminobenzene
D) 2,5-Dichloroanisole
A) 3,6-Dichloroaniline
B) 2,5-Dichloroaniline
C) 2,5-Dichloroaminobenzene
D) 2,5-Dichloroanisole
Question
What orbitals are used to form the bond indicated in the following molecule? 
A) Csp2 Csp2
B) Csp2 C2p
C) C2p C2p
D) Csp3 Csp3
A) Csp2 Csp2
B) Csp2 C2p
C) C2p C2p
D) Csp3 Csp3
Question
What is the correct assignment of the names of the following fused aromatic compounds? ![<strong>What is the correct assignment of the names of the following fused aromatic compounds? </strong> A) I = naphthalene; II = anthracene; III = phenanthrene. B) I = naphthalene; II = phenanthrene; III = anthracene. C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene. D) I = anthracene; II = naphthalene; III = phenanthrene. <div style=padding-top: 35px>](https://storage.examlex.com/TB5871/11ea9088_70ba_4954_aec7_af90beedcffb_TB5871_00_TB5871_00_TB5871_00_TB5871_00_TB5871_00_TB5871_00_TB5871_00.jpg)
A) I = naphthalene; II = anthracene; III = phenanthrene.
B) I = naphthalene; II = phenanthrene; III = anthracene.
C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene.
D) I = anthracene; II = naphthalene; III = phenanthrene.
A) I = naphthalene; II = anthracene; III = phenanthrene.
B) I = naphthalene; II = phenanthrene; III = anthracene.
C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene.
D) I = anthracene; II = naphthalene; III = phenanthrene.
Question
What is the correct assignment of the names of the following substituted benzenes? 
A) I = Styrene; II = aniline; III = anisole.
B) I = Toluene; II = anisole; III = styrene.
C) I = Styrene; II = anisole; III = phenol.
D) I = Toluene; II = aniline; III = anisole.
A) I = Styrene; II = aniline; III = anisole.
B) I = Toluene; II = anisole; III = styrene.
C) I = Styrene; II = anisole; III = phenol.
D) I = Toluene; II = aniline; III = anisole.
Question
What is the IUPAC name of the following compound? 
A) 2-Nitro-5-carboxychlorobenzene
B) 2-Chloro-4-carboxynitrobenzene
C) 2-Chloro-1-nitro-4-benzoic acid
D) 3-Chloro-4-nitrobenzoic acid
A) 2-Nitro-5-carboxychlorobenzene
B) 2-Chloro-4-carboxynitrobenzene
C) 2-Chloro-1-nitro-4-benzoic acid
D) 3-Chloro-4-nitrobenzoic acid
Question
What is the correct assignment of the names of the following aromatic heterocycles? 
A) I = pyridine; II = pyrimidine; III = furan.
B) I = pyrimidine; II =pyrrole; III = furan.
C) I = pyridine; II = pyrrole; III = furan.
D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
A) I = pyridine; II = pyrimidine; III = furan.
B) I = pyrimidine; II =pyrrole; III = furan.
C) I = pyridine; II = pyrrole; III = furan.
D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
Question
Question
What is the correct assignment of the names of the following substituted benzenes? 
A) I = Phenol; II = anisole; III = toluene.
B) I = Benzaldehyde; II = phenol; III = anisole.
C) I = Benzaldehyde; II = phenol; III = toluene.
D) I = Phenol; II = anisole; III = styrene.
A) I = Phenol; II = anisole; III = toluene.
B) I = Benzaldehyde; II = phenol; III = anisole.
C) I = Benzaldehyde; II = phenol; III = toluene.
D) I = Phenol; II = anisole; III = styrene.
Question
Which of the following heterocycles is not aromatic? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
What is the IUPAC name of the following compound? 
A) 3-Bromo-1-chloro-4-toluene
B) 2-Bromo-4-chlorotoluene
C) 4-Chloro-2-bromo-1-toluene
D) 2-Bromo-4-chloroanisole
A) 3-Bromo-1-chloro-4-toluene
B) 2-Bromo-4-chlorotoluene
C) 4-Chloro-2-bromo-1-toluene
D) 2-Bromo-4-chloroanisole
Question
Question
What is the IUPAC name of the following compound? 
A) 1-Chloro-4-ethyl-3-propylbenzene
B) 1-Chloro-4-ethyl-5-propylbenzene
C) 4-Chloro-1-ethyl-2-propylbenzene
D) 4-Chloro-2-propyltoluene
A) 1-Chloro-4-ethyl-3-propylbenzene
B) 1-Chloro-4-ethyl-5-propylbenzene
C) 4-Chloro-1-ethyl-2-propylbenzene
D) 4-Chloro-2-propyltoluene
Question
Which of the following compounds is aromatic? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
Why is the following compound not aromatic? 
A) It has 4n pi electrons.
B) It is not cyclic.
C) It has 4n+2 pi electrons.
D) The electron system is not continuous.
A) It has 4n pi electrons.
B) It is not cyclic.
C) It has 4n+2 pi electrons.
D) The electron system is not continuous.
Question
What orbitals are used to form the indicated bond? 
A) sp3
B) sp2
C) p
D) sp3 and sp2
A) sp3
B) sp2
C) p
D) sp3 and sp2
Question
Question
Which of the following compounds is not aromatic? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
How many different proton signals would the following compound show in its 1H NMR spectrum? 
A) 1
B) 3
C) 5
D) 6
A) 1
B) 3
C) 5
D) 6
Question
What is the correct structure for 1-bromo-2,4-dimethoxybenzene? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
Which of the following ions is aromatic? 
A) Only I and II
B) Only II and III
C) Only III and IV
D) Only II and IV
A) Only I and II
B) Only II and III
C) Only III and IV
D) Only II and IV
Question
What compound is consistent with the following 1H NMR spectrum? 
A) phenol
B) anisole
C) 4-bromoanisole
D) 4-bromotoluene
A) phenol
B) anisole
C) 4-bromoanisole
D) 4-bromotoluene
Question
Which of the following compounds is not aromatic? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
What is the name of the following compound? 
A) 2,6-dimethylbenzene
B) 5-methyltoluene
C) anisole
D) 1,3-dimethylbenzene
A) 2,6-dimethylbenzene
B) 5-methyltoluene
C) anisole
D) 1,3-dimethylbenzene
Question
What is the correct structure for toluene? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
What is the name of the following compound? 
A) meta-bromophenol
B) para-hydroxybenzene
C) 3-bromoanisole
D) 6-methoxy-2-bromobenzene
A) meta-bromophenol
B) para-hydroxybenzene
C) 3-bromoanisole
D) 6-methoxy-2-bromobenzene
Question
What is the correct structure for anisole? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
Why is the following compound not aromatic? 
A) It has 4n electrons.
B) It is not cyclic.
C) It has 4n+2 electrons.
D) The electron system is not continuous.
A) It has 4n electrons.
B) It is not cyclic.
C) It has 4n+2 electrons.
D) The electron system is not continuous.
Question
Which of the following compounds is aromatic? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
What is the correct structure for aniline? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
Question
What is the correct structure for para-bromotoluene? 
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
Question
What orbitals are used to form the indicated bond? 
A) sp3
B) sp2
C) p
D) sp3 and sp2
A) sp3
B) sp2
C) p
D) sp3 and sp2
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Deck 17: Benzene and Aromatic Compounds
1
Which of the following molecules has the most acidic hydrogen atoms?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
III
2
Which of the following ions is aromatic?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
I
3
How many 13CNMR signals does the following compound exhibit?
A) 4
B) 5
C) 6
D) 8
A) 4
B) 5
C) 6
D) 8
6
4
Which of the following statements about benzene is true?
A) Benzene is a saturated hydrocarbon.
B) Benzene undergoes addition reactions.
C) Benzene has five degrees of unsaturation.
D) Benzene undergoes substitution reactions.
A) Benzene is a saturated hydrocarbon.
B) Benzene undergoes addition reactions.
C) Benzene has five degrees of unsaturation.
D) Benzene undergoes substitution reactions.
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5
What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives?
A) I = 3 signals; II = 3 signals; III = 2 signals.
B) I = 3 signals; II = 4 signals; III = 2 signals.
C) I = 6 signals; II = 6 signals; III = 6 signals.
D) I = 3 signals; II = 4 signals; III = 3 signals.
A) I = 3 signals; II = 3 signals; III = 2 signals.
B) I = 3 signals; II = 4 signals; III = 2 signals.
C) I = 6 signals; II = 6 signals; III = 6 signals.
D) I = 3 signals; II = 4 signals; III = 3 signals.
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6
Rank the following compounds in order of decreasing acidity, starting with the most acidic.
A) I > II > III
B) III > II > I
C) III > I > II
D) I > III > II
A) I > II > III
B) III > II > I
C) III > I > II
D) I > III > II
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7
What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150 2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm.
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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8
Which of the following is not one of the Hückel's criteria for aromaticity?
A) The molecule must be cyclic.
B) The molecule must be planar.
C) The molecule must be completely conjugated.
D) The molecule must have 4n pi electrons.
A) The molecule must be cyclic.
B) The molecule must be planar.
C) The molecule must be completely conjugated.
D) The molecule must have 4n pi electrons.
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9
What is the IUPAC name of the following compound?
A) 3,6-Dichloroaniline
B) 2,5-Dichloroaniline
C) 2,5-Dichloroaminobenzene
D) 2,5-Dichloroanisole
A) 3,6-Dichloroaniline
B) 2,5-Dichloroaniline
C) 2,5-Dichloroaminobenzene
D) 2,5-Dichloroanisole
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10
What orbitals are used to form the bond indicated in the following molecule?
A) Csp2 Csp2
B) Csp2 C2p
C) C2p C2p
D) Csp3 Csp3
A) Csp2 Csp2
B) Csp2 C2p
C) C2p C2p
D) Csp3 Csp3
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11
What is the correct assignment of the names of the following fused aromatic compounds?
A) I = naphthalene; II = anthracene; III = phenanthrene.
B) I = naphthalene; II = phenanthrene; III = anthracene.
C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene.
D) I = anthracene; II = naphthalene; III = phenanthrene.
A) I = naphthalene; II = anthracene; III = phenanthrene.
B) I = naphthalene; II = phenanthrene; III = anthracene.
C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene.
D) I = anthracene; II = naphthalene; III = phenanthrene.
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12
What is the correct assignment of the names of the following substituted benzenes?
A) I = Styrene; II = aniline; III = anisole.
B) I = Toluene; II = anisole; III = styrene.
C) I = Styrene; II = anisole; III = phenol.
D) I = Toluene; II = aniline; III = anisole.
A) I = Styrene; II = aniline; III = anisole.
B) I = Toluene; II = anisole; III = styrene.
C) I = Styrene; II = anisole; III = phenol.
D) I = Toluene; II = aniline; III = anisole.
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13
What is the IUPAC name of the following compound?
A) 2-Nitro-5-carboxychlorobenzene
B) 2-Chloro-4-carboxynitrobenzene
C) 2-Chloro-1-nitro-4-benzoic acid
D) 3-Chloro-4-nitrobenzoic acid
A) 2-Nitro-5-carboxychlorobenzene
B) 2-Chloro-4-carboxynitrobenzene
C) 2-Chloro-1-nitro-4-benzoic acid
D) 3-Chloro-4-nitrobenzoic acid
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14
What is the correct assignment of the names of the following aromatic heterocycles?
A) I = pyridine; II = pyrimidine; III = furan.
B) I = pyrimidine; II =pyrrole; III = furan.
C) I = pyridine; II = pyrrole; III = furan.
D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
A) I = pyridine; II = pyrimidine; III = furan.
B) I = pyrimidine; II =pyrrole; III = furan.
C) I = pyridine; II = pyrrole; III = furan.
D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
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15
Which of the following statements about the structure of benzene is not true?
A) Benzene is planar.
B) Benzene has three short double bonds alternating with three longer single bonds.
C) The electrons in the pi bonds are delocalized around the ring.
D) Benzene has six pi electrons.
A) Benzene is planar.
B) Benzene has three short double bonds alternating with three longer single bonds.
C) The electrons in the pi bonds are delocalized around the ring.
D) Benzene has six pi electrons.
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16
What is the correct assignment of the names of the following substituted benzenes?
A) I = Phenol; II = anisole; III = toluene.
B) I = Benzaldehyde; II = phenol; III = anisole.
C) I = Benzaldehyde; II = phenol; III = toluene.
D) I = Phenol; II = anisole; III = styrene.
A) I = Phenol; II = anisole; III = toluene.
B) I = Benzaldehyde; II = phenol; III = anisole.
C) I = Benzaldehyde; II = phenol; III = toluene.
D) I = Phenol; II = anisole; III = styrene.
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17
Which of the following heterocycles is not aromatic?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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18
What is the IUPAC name of the following compound?
A) 3-Bromo-1-chloro-4-toluene
B) 2-Bromo-4-chlorotoluene
C) 4-Chloro-2-bromo-1-toluene
D) 2-Bromo-4-chloroanisole
A) 3-Bromo-1-chloro-4-toluene
B) 2-Bromo-4-chlorotoluene
C) 4-Chloro-2-bromo-1-toluene
D) 2-Bromo-4-chloroanisole
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19
Which of the following is not a criterion for antiaromaticity?
A) The molecule must be cyclic.
B) The molecule must have (4n + 2) pi electrons.
C) The molecule must be planar.
D) The molecule must be completely conjugated.
A) The molecule must be cyclic.
B) The molecule must have (4n + 2) pi electrons.
C) The molecule must be planar.
D) The molecule must be completely conjugated.
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20
What is the IUPAC name of the following compound?
A) 1-Chloro-4-ethyl-3-propylbenzene
B) 1-Chloro-4-ethyl-5-propylbenzene
C) 4-Chloro-1-ethyl-2-propylbenzene
D) 4-Chloro-2-propyltoluene
A) 1-Chloro-4-ethyl-3-propylbenzene
B) 1-Chloro-4-ethyl-5-propylbenzene
C) 4-Chloro-1-ethyl-2-propylbenzene
D) 4-Chloro-2-propyltoluene
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21
Which of the following compounds is aromatic?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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22
Why is the following compound not aromatic?
A) It has 4n pi electrons.
B) It is not cyclic.
C) It has 4n+2 pi electrons.
D) The electron system is not continuous.
A) It has 4n pi electrons.
B) It is not cyclic.
C) It has 4n+2 pi electrons.
D) The electron system is not continuous.
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23
What orbitals are used to form the indicated bond?
A) sp3
B) sp2
C) p
D) sp3 and sp2
A) sp3
B) sp2
C) p
D) sp3 and sp2
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24
Where do the protons in benzene appear in the 1H NMR spectrum?
A) Around 1600 cm-1
B) Around 120 ppm
C) Around 0 ppm
D) Around 7 ppm
A) Around 1600 cm-1
B) Around 120 ppm
C) Around 0 ppm
D) Around 7 ppm
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25
Which of the following compounds is not aromatic?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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26
How many different proton signals would the following compound show in its 1H NMR spectrum?
A) 1
B) 3
C) 5
D) 6
A) 1
B) 3
C) 5
D) 6
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27
What is the correct structure for 1-bromo-2,4-dimethoxybenzene?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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28
Which of the following ions is aromatic?
A) Only I and II
B) Only II and III
C) Only III and IV
D) Only II and IV
A) Only I and II
B) Only II and III
C) Only III and IV
D) Only II and IV
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29
What compound is consistent with the following 1H NMR spectrum?
A) phenol
B) anisole
C) 4-bromoanisole
D) 4-bromotoluene
A) phenol
B) anisole
C) 4-bromoanisole
D) 4-bromotoluene
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30
Which of the following compounds is not aromatic?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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31
What is the name of the following compound?
A) 2,6-dimethylbenzene
B) 5-methyltoluene
C) anisole
D) 1,3-dimethylbenzene
A) 2,6-dimethylbenzene
B) 5-methyltoluene
C) anisole
D) 1,3-dimethylbenzene
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32
What is the correct structure for toluene?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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33
What is the name of the following compound?
A) meta-bromophenol
B) para-hydroxybenzene
C) 3-bromoanisole
D) 6-methoxy-2-bromobenzene
A) meta-bromophenol
B) para-hydroxybenzene
C) 3-bromoanisole
D) 6-methoxy-2-bromobenzene
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34
What is the correct structure for anisole?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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35
Why is the following compound not aromatic?
A) It has 4n electrons.
B) It is not cyclic.
C) It has 4n+2 electrons.
D) The electron system is not continuous.
A) It has 4n electrons.
B) It is not cyclic.
C) It has 4n+2 electrons.
D) The electron system is not continuous.
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36
Which of the following compounds is aromatic?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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37
What is the correct structure for aniline?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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38
Which of the following statements about the molecular orbital (MO) theory is true?
A) When two p orbitals of similar phase overlap side-by-side, a * antibonding molecular orbital is formed.
B) When two p orbitals of opposite phase overlap side-by-side, a bonding molecular orbital is formed.
C) A bonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed.
D) A * antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed.
A) When two p orbitals of similar phase overlap side-by-side, a * antibonding molecular orbital is formed.
B) When two p orbitals of opposite phase overlap side-by-side, a bonding molecular orbital is formed.
C) A bonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed.
D) A * antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed.
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39
What is the correct structure for para-bromotoluene?
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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40
What orbitals are used to form the indicated bond?
A) sp3
B) sp2
C) p
D) sp3 and sp2
A) sp3
B) sp2
C) p
D) sp3 and sp2
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